1. Field of the Invention
This invention relates to novel intermediate compounds, and to methods for their preparation and use as intermediates in the preparation of other useful compounds. More particularly, this invention relates to novel oxazoline compounds, their preparation and methods for using such compounds in the preparation of various cycloalkane-1,2-dione, cycloalkane-1,2-dione oxime and cyclohexane-1,2-dione dioxime derivatives.
2. Brief Description of the Prior Art
It has been reported in the literature that treatment of cycloalkanone compounds with oxygen in the presence of an alkali metal halide catalyst causes ring cleavage and the production of the corresponding ketomonocarboxylic acid. For example, U.S. Pat. No. 3,387,026 describes a procedure in which 2-methyl-cyclohexanone is treated with oxygen gas in the presence of potassium fluoride or lithium fluoride to provide 6-oxoheptanoic acid.
Other prior art has reported that treatment of cycloalkanone compounds with oxygen gas in the presence of an alkali metal hydroxide or alkoxide will provide the corresponding cycloalkane-1,2-dione compound. For example, the references, U.S. Pat. No. 4,018,827, and Rao, Durvasula V, et al., "Base Catalyzed Autoxidation of Cyclic Ketones", J. Org. Chem. vol. 44, No. 3 pp. 456-458, (1979) describe a process in which cyclohexanone is treated with oxygen gas in the presence of potassium butoxide to provide cyclohexanone-1,2-dione. While the above process can be used to prepare cycloalkane-1,2-dione compounds, it suffers from several disadvantages. The reaction yields are relatively low, and vary over a wide range, thus, the process is not very efficient. Furthermore, the process does not appear to be applicable to the preparation of 1,2-dione derivatives of cycloalkanone compounds having more than six ring carbon atoms. For example, Rao, Durvasula V., et al, supra disclose that use of cycloheptanone reactants in the process provides tricyclic compounds having ester and keto functions.